Looks are so Deceiving
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Appearances Can Be Deceiving free porn video
Appearances can be deceiving by [email protected]
Somewhat true story. Based on some real events but also has some a bit of
flourishment for flavor in partial sections. Involves teen age cross
dressing and some light sex. I hope you enjoy.
I will just say it up front. My name is Darrek, I am a mid 30's man, I
sometimes dress as a woman, and I like cock. Am I gay, well that is
subjective. I do still enjoy being with a woman however I like men a bit
more. So maybe I am considered somewhat bi-sexual. Who knows and I really
don't care what label is put on me. I am happy and that is what matters.
Allow me to regale the story of some of the high points of my interesting
life.
Oddly enough, it wasn't normal per se but not necessarily bad. I was very
young when my parents divorced and my sister and I ended up with my mom.
I don't remember it all and when I got older, I rarely saw my real dad so
I didn't even consider him part of the family. My mom dated now and again
but never anything too serious. Ok, let me be blunt. She liked to fuck.
Not nympho style, like everyday and all that but she liked casual dating
I should say. Was she a whore? I don't know but she was a great mother
and that is what counts.
My sister, Sarah, she was cute in a plain way and kind of shy. Kind of
the bookworm type but nice and we always got along pretty well. She
didn't date all that much that I recall but she was fine with that. I
remember a couple steady boyfriends but they didn't last more than a few
months at a time. Her longest was a year and change but they split up
when he moved away after high school to go to college. I think they still
talk now and then.
As for myself, I knew early on I was different. I could just sense it. I
was girl watching like the others but also watched the boys too. Sure I
thought it was wrong and strange and tried to stop but it didn't work out
that way. Eventually I quit trying and just hid it. But I did tell my
sister so I could at least have someone to talk to about it. She was cool
with it as long as I was which worked out well. We were always like that.
Open with each other and free to talk about anything. Hell I practically
knew about her first sexual encounter before the guy did. Well, she told
me before the date that she was going to do something. And she did.
Didn't go all the way but she blew him. She must've really liked him
considering how shy she was. I guess she got over that for at least that
evening.
I also learned I had a penchant for girly clothes too. Wasn't by
accident, I asked Sarah if I could try some panties on one day and she
agreed. Why I did it I still am not sure. Maybe I loved how they looked
on the girls and was curious. Either way, it started there and is still
going today. Yes there were times I stopped for a while but never
entirely. Sometimes she would dress me all up and we would spend the
afternoon girl talking. That was strange but we enjoyed it. My girl name
was/is Jill which I chose because of a real gorgeous girl I met once. She
turned me down but still she was very cute and stuck in my mind.
I was an early teenager, 14, when I began to get the urge to be with a
guy. I had considered it before but it was around that time that I gave
it serious thought. I was real curious and tried to think of ways to make
it happen. I am not shy at all but I had to be careful, I understood that
for various reasons. I contemplated a couple friends of mine but knew no
matter how good of friends we were, they would not go for it. So I ruled
them out. Sarah tried to help but didn't know anyone at all that could
assist in this.
So for a while we worked on that. During that time, my cross-dressing was
getting refined and more exact. I could sometimes pull off a real girl
but not quite. But close. The voice was the toughest thing to replicate.
I got to a decent point and practiced it yet it was just a bit off. I
would have to deal with that. Most every other aspect I got down well.
Makeup was a challenge but Sarah, as she did with everything else, aided
in that. I am so glad to have a sister like her. Mom was still unaware
but later when she found out, she didn't really care. As long as it was
good for me, she was fine. A little shocked but not terribly. Moms always
know their children too well.
Finally it happened for me though about a year later. It was a Halloween
party Sarah got invited to and she was allowed to bring a friend or two.
We talked it over and she let them know her friend Jill would be coming.
I had gone in public now and again but not like this. I was a little
nervous but not tremendously. I was more excited than anything. And no
one there would know who I was really since it was not in town, but about
an hour away. A couple weeks before the party is when I sprung my secret
on mom. Figured she should know and we had a talk and all was fine. I
think it took some time to really sink in but when she saw me with Sarah
before we left, it hit her. I was in a cheerleader outfit that Sarah had
bought when she thought about trying out briefly. She wore it once and
never again so she gave it to me. I was thrilled! I also have to say I
looked not too bad in it.
We get to the party and start mingling. As I thought, we knew no one
there except she knew the host and her sister. Worked for us. The party
was chaperoned by the parents but it encompassed the whole house more or
less so when we wanted to have good fun, we went to the basement. The
sisters had snuck in some beers and we would go down there now and again
to have some. We were careful and the parents were pretty cool. I think
they knew and were keeping an eye on things myself. I also think the
father liked the young girls because I would catch him stealing a glance
now and again. I thought it was weird but who could blame him. There were
some cute girls there and not all were dressed in sedate outfits.
The party was actually fun. I talked as little as I had to just to be
sure but no one seemed to be the wiser. It was pretty crowded too at its
high point so getting lost in it was easy should I have need to. I
actually got hit on a number of times. That was a first and I really
didn't know how to react but I loved it. I was flirty as I could be and
with my desire, some of the beer, and the great outfit I had on, I knew I
would do something this night. It was a couple hours into it when one guy
in particular caught my interests. Aaron was his name. He was cute, well
spoken, and a little shy but not terribly, and alone. He sort of hit on
me earlier but left when I got distracted by someone else trying to talk
to me. I found him again and chatted some more. He did most of the
talking and he didn't seem to notice anything too odd when I did so that
was good. Maybe because it was a little loud or he was drinking a little
too.
We learned a little about each other although most of what I said was a
lie. Maybe he was lying too but it didn't matter. He was nice, polite,
and cute with a nice butt. We went downstairs where the real party was
(and also the make-out spot) and started talking then moved to kissing. I
had never kissed anyone and he knew that. That much wasn't a lie but we
worked through it. I really liked it. It was great! And no one was
pointing and staring because nearby two other couples were doing the same
thing in the darkened section of the basement. As we made out, our hands
roamed around each other. I wasn't too worried. I knew my ?breasts? would
pass a casual massage (thanks to Sarah again) as long as no up close
inspection was done. And if he kept his hands out of my panties, all
would be good. So I made sure he did.
I took the initiative and unzipped his pants. He got nervous and said
maybe we shouldn't and I asked if he really wanted a cute girl to stop
what she was about to do. That didn't take long to process because I was
stroking him the whole time. His cock was bigger than mine but not huge
by any means. It was the only one other than mine I had really touched
and was enjoying it but I knew I wanted more. Actually I wanted a lot
more but I had to settle for sliding off the couch to my knees in front
of him and taking his dick in my mouth. From his moan, I guessed he liked
it. I only had a vague notion of what to do, even though I have been
practicing and Sarah gave some pointers from her one time but I figured
it out soon enough.
I heard the whispers from the nearest couple and they seemed happy about
it with the quiet encouragement they were giving. As I was bobbing up and
down, and enjoying the hell out of it, I was picturing how I must look.
On my knees in a cheerleaders outfit giving head to some guy I just met
at a party. That made it even better. I was 15, a guy, pretending to be a
girl and getting away with it in front of others. I was in my own world.
I couldn't get enough of his cock. I got lost in the mere sensation of
having a guy's cock sliding in and out of my mouth. It was heaven and I
knew I would want more of this.
I do not know how long it lasted. I wanted it to go on forever. If I
could suck cock likes this as much as possible, I would. I was hooked.
And I think I started going at him a little bit more because soon enough,
I got rewarded with him shooting his load in my mouth. I wasn't ready for
that and I gagged and pulled off getting the last bit on my face and in
my hair (wig).
He started apologizing but I was resting back on my heels with a smile on
my face. He got me a towel to clean up with and when we were ready, we
left. The small crowd that was down here as we walked through gave us
knowing smiles and small cheers. I just grinned back as I took his hand
and went upstairs. On the way up, I took that hand of his and put it up
under my skirt on my ass and winked at him. He returned it and we went
back to normal as we got to the top of the stairs.
The rest of the party we were together. Dancing, chatting, flirting,
kissing, having a good time. At the end of the evening, I got his number
and promised to call. On the way home Sarah told me she heard what
happened downstairs. I guess it got around. I didn't care. I was happy,
Aaron was happy, and Sarah was happy for me. It was a good night all in
all and I regret none of it.
Stayed tuned for more of the adventures of Jill. Some good, some bad, all
interesting (at least to me).
Fawn
- 12.11.2021
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